This chapter continues to explore the depiction of Herod’s domestic strife, and turns to the executions of Herod’s sons. This is a rare case where we have a separate fragment of Nicolaus, and thus can check Josephus’ censure of his predecessor’s account: the criticisms are not borne out, and Josephus’ accounts instead exhibit many Damascene traits. The executions, moreover, are a turning point in Herod’s decline from δραστήριος to ἄπορος, in which he is shown to have now forgotten piety and justice. Furthermore, because Nicolaus himself was intimately bound up with these events, he here encountered new challenges in his narrative as he became one of the principal actors. Thus, not only do we see in these trials the further development of, we argue, Nicolaus’ depiction of the king’s descent into tyranny, but also a sustained exploration of what it meant to be an adviser to such a monarch, and more generally what it meant to be a φίλος to king and emperor alike in the Augustan world.